Ten tips for landing enterprise customers

Signing up enterprise customers can be challenging for startups. Everyone wants to land a big contract with a large, solid company, but it can be a bit of a black box to figure out how to do it, or whether enterprise prospects should be approached differently.

It’s all the more important because there’s a lot at stake. An enterprise contract can be many times bigger than a company’s average deal. The last thing anyone wants is for a big deal to fall through because some tiny detail was overlooked or because someone forgot to answer an email.

As we have gained more experience signing up enterprise customers, I have begun to reflect on what it’s taken to win enterprise customers.

Yes, a different approach is needed. Everything about an enterprise deal is bigger – that’s why going after enterprise firms is sometimes called ‘whale hunting.’ There are more people to sell to, more meetings to have, more steps to go through, more security questions, more to think about overall. Everything takes more time and requires more patience.

But sometimes the biggest obstacle is just getting over the mental block of going after a big customer. That’s because as long as you are prepared and diligent and responsive, it’s ultimately just like closing any other deal.

What I’m presenting here is a checklist of things I think it’s important to consider as we look for new customers and negotiate agreements with them. Experience has shown me that checking off every item on this list will make successfully signing up new enterprise customers much easier.

1. Work on your introductions

Potential enterprise customers don’t appear out of thin air. Yes, your sales team can make cold calls, but the best prospects are the ones who are introduced to you by colleagues, partners or existing customers.

For that reason, it pays to be deliberate about seeking out introductions.

To give one example, we recently signed up a big new customer after having been introduced to them at the Adobe Summit in March 2023.

On the surface, it seemed simple enough: One of our partners, a large service integrator, brought someone from the company we eventually signed up to our booth at the Adobe Summit. That led to a discussion that ended in us signing them up several months later.

The reality is more complicated. It actually took years of relationship-building before that introduction could happen.

The person from our existing partner who brought the prospect over to us had to know our work well enough to be confident that we had a solution to the prospect’s email marketing problems. Their credibility was on the line; if Knak hadn’t been up to the task, our partner would have looked bad.

That credibility was built up over time; our partner had to be able to vouch for the fact that their customers (the ones they have in common with us) liked Knak.

There are really no shortcuts; building relationships and networks takes time. So work on getting to a place where useful introductions can be made.

2. Seize opportunities when they arise

An introduction to a potential enterprise customer is very valuable; you can’t just let it ride. So whenever an introduction is made, you have to be prepared to seize the opportunity.

That means being prepared. You want to make sure your potential client is introduced to the right person at your company, someone with a good attitude and enough savvy to understand what’s at stake.

That’s not a given.

What if the only person at your booth when the introduction is made is a brand-new marketer who doesn’t grasp the prospect’s potential? What if they forget to get the prospect’s contact info or come across as bored because it’s the end of a long day?

The possibility of things like that happening sends shivers down my spine.

In the example from the Adobe Summit, it took us a moment to twig to the immense potential of the deal. Only after I listened to a recording of the first contact between the prospect and Knak – a call involving two new Knak sales people – did I realize how many potential Knak users they were talking about. That’s when I got really excited.

3. Be excited about the problem you are going to solve

It’s very important, as you engage with a potential enterprise customer, to build a rapport with them.

That means getting to know them and their needs, of course.

But it also means getting excited about the problems you are going to solve for them, right from the first contact.

Why? Because excitement is built on confidence.

I got excited about that Adobe Summit prospect because I knew immediately that Knak could be of huge benefit to them. Solving problems like the ones they had is our very reason for existing.

It’s very important that everyone from Knak show the same excitement and confidence when talking to a potential new customer. It gives energy to discussions.

To give your excitement and confidence a boost, you have got to demonstrate that you are listening to your potential customer. That means speaking their language and understanding their jargon.

Words matter. Nuances matter.

If you don’t nail the buyer’s technical jargon immediately, it will sound to them like you’re not listening, and your excitement and confidence will come across as hype.

I know because we’ve made mistakes in the past. We’ve failed to show passion and energy, we’ve failed to nail down a potential client’s technical jargon. And as a result they did not take us seriously. Deals we were working on got stalled as the potential buyer of our services became disengaged.

Luckily, you can correct this kind of mistake if you catch it quickly enough.

4. Use contacts and connections judiciously

To move a deal along, to bring it back to life after it’s stalled, or to put things back on trajectory after a bad start, it may be necessary to use contacts or connections you have at the prospective client’s company.

Ideally, you should never get yourself into a situation where you have to jump-start stalled talks. But in a pinch, reaching out to contacts is an option.

When our talks with the new prospect stalled, I reached out to someone I knew there. I sent them a one-page summary of their problem (to demonstrate that we understood it) along with an explanation of why Knak was a solution to their problem. That was enough to get the ball rolling again.

5. Demonstrate how you can solve something the buyer cares about

One way to demonstrate that you are listening to a prospective customer is to show them how you can provide a solution to something they care about.

Our new prospect, for example, cared deeply about one particular issue. We had been working for a year on developing a feature that addressed that very issue, but it was not yet ready for release.

Because it was still being developed and not yet ready for market, our Sales team was not aware they could be promoting this feature. Luckily, I knew about it and was able to let the prospect know it was going to be ready in short order.

And to prove it was close to release, we organized a call in which the feature developers were able to explain it in technical terms to the prospect’s technical people.

That gave the prospect even more confidence in us because it showed that we understood their pain point and were close to a solution that would help them tremendously.

It pays to know who in your company is the best person to sell to a particular prospective customer.

Developers don’t usually participate in the sales process, but in this case they were the right people to involve.

6. Meet in person

Zoom is great, but nothing beats real, in-person meetings to seal deals.

In-person meetings are a must if you are going to get to know enterprise customers and their needs, and if they are going to get to know and trust you.

If the meetings involve travel, so be it; the investment is worth it, particularly for bigger contracts. But sometimes you don’t have to go out of your way. You may find your prospective customer is attending the same conference as you. Make a point of getting together. Even better, introduce them to your existing customers.

7. Have patience

As much as you’d like to have everything signed, sealed and delivered by tomorrow, it’s not going to happen. For a variety of reasons, not the least of which is the need to build relationships and trust, deals take time to mature.

This is especially true when you are dealing with enterprise companies, where procurement processes can be very involved and where several people at different levels have to be convinced before signing off.

We’ve given potential customers the option of canceling a contract after 90 days without penalty; that gives people enough time to see how valuable Knak can be for them. And if that still isn’t enough, we will introduce them to another company that is already using Knak and let them talk to each other on their own.

You need to jump through the hoops. And when you come up against roadblocks or problems, you just need to persevere and find a solution.

So be prepared to run a marathon. As you do, keep focused on what the customer cares about and what success looks like to them. Then do what you can to get them there – with a smile.

8. Be prepared to adapt

Our contract with the new customer was big, but it contained a twist we had never seen before. To win the contract, we had to change our pricing model to accommodate that twist.

Our pricing model had been based on the number of Knak users at a client company.

But the new customer told us that while a core team of marketers would use Knak almost daily, a much bigger group would use Knak only on occasion, and an even bigger number of people would use Knak only once or twice a year.

Our new customer understandably did not want to pay full price for people who would use Knak only occasionally.

So we got creative and adapted our pricing model to suit their needs.

9. Build relationships

In my mind, there are three kinds of business relationships.

The first is a transactional relationship, where money is exchanged for a good or service. Nothing else is expected or required, and the parties go their separate ways after the deal is done.

The second is a partnership relationship. Here, each party cares about the success of the other because if they both succeed they can keep doing business with each other.

The third and most powerful relationship is a personal relationship. In addition to caring about the transaction and the continued success of the business that’s buying from you, you recognize the person you are dealing with as a fellow human.

A personal relationship is very powerful because it engenders trust. The more you get to know the people you deal with as humans, the more you can build those bonds of trust. So work on creating personal relationships; it will help cement deals.

10. Deliver what you promised

The process of bringing in a new enterprise client does not end when you sign a contract. To maintain a good working relationship, you have to make sure to deliver what you promised.

That starts with making sure they know how to use the product so they can get the most out of it. And of course customer service is important so you can deal quickly with questions, problems and issues that arise.

Bonus tip

Signing up enterprise customers is not easy.

But I enjoy a challenge, and it’s very rewarding to see the results after you’ve put in the hard work.

So here’s one final checklist item: After you’ve signed a deal, celebrate it with your team.

It’s good – even necessary – to pat yourself on the back occasionally.